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This is for PDTaxPlease provide some direction for the

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Client letter facts: A client walks into your office and states, he is seeking to get into real estate. He wants to purchase houses, fix them and then resell the houses, hopefully at a profit. He is going to do, hopefully, 4 to 5 a year, and hopes to make around $40,000 per house. He is using outside contractors and his own help to make the modifications to the house to increase the value. He would like to know, what is the best entity type, he has one or two other people that would like to be part of the operation, but he states, he is not sure and if they came on, which offers the most flexibility regarding profit and loss sharing. In addition, he would like to know, how is the gain going to be dealt with, ordinary or capital gains.

Hi again. I know how I would set things up, which is a hybrid of the standard solution.

The first entity choice depends on the financing. It will be hard to use an entity for flips if you need bank financing. Banks prefer to lend residential mortgage money to individuals. Please confirm how the properties will be bought first. This may drive part 2.

Second, using partners in the flip or rehab venture normally should be done in an LLC. Flexibility in income distribution (as a partnership) makes an LLC the choice for partners when payout flexibility is the key. A corp might also work well here. Depends on part 1 and the income payout/mix of investor partners and hammer swinger partners.

Third, your client should set up his interest in his own management company. Since it will have few if any assets at first (more on that later), a single-member LLC, S corp or even a C corp works here. Your client works for w-2 wage and perks for some of the income, and the rest flows to him without Social Security taint or is retained in a C corp to take advantage of its marginal rates.

Lastly, the gains are not capital gains, especially if several flip sales are reported in a calendar year. IRS will consider that income from sales of inventory, and tax it as ordinary income.

Capital gain treatment comes for individuals who buy and hold one for a year before selling. They get capital gain treatment. If they live in it for two years, they get gain exclusion from sale of a principal residence. But if they flip it in 90 days, and do another one, and never live there, it's sale of inventory and ordinary income.

Thanks again for asking for me. Hope that covers it for you. Ask follow up if you need anything.

The issue hinges on 1221(a) classification of a capital asset. That's the code section, but the dealer issue is case law-driven.

The NYSSCPA magazine, The CPA Journal, had a good discussion of the issue in 2007. http://www.nysscpa.org/cpajournal/2007/607/essentials/p44.htm is the link to that article. I will paraphrase from that content:

Under IRC section 1221(a)(1), real property “held by the taxpayer primarily for sale to customers in the ordinary course of a trade or business” is not a capital asset. As defined by the Fifth Circuit, “business” means:

The work, notwithstanding disguise in spelling and pronunciation, means busyness; it implies that one is kept more or less busy, that the activity is an occupation. It need not be one’s sole occupation, nor take all his time. It may be only seasonal, and not active the year round. It ordinarily is implied that one’s own attention and effort are involved, but the maxim qui facit per alium facit per se applies, and one may carry on a business through agents whom he supervises (C.P. Snell v. Comm’r, CA-5, 38-2 USTC para.9417, 97 F2d 891).

Therefore, any gain or loss on real property that is held primarily for sale will be treated as ordinary gain or loss. The word “primarily” in this context means “of first importance,” or “principally” [Malat v. Riddell, 383 US 569, 17 AFTR2d 604 (1966)]. If the property is not determined to be held for sale, then it will receive capital gains treatment.

WENDELL V. AND SHARON T. GARRISON, Petitioners v. COMMISSIONER OF INTERNAL REVENUE, Respondent . Case Information: Code Sec(s): 1221; 1401; 61; 6651; 7491 Docket: Docket Nos. 19988-07, 19989-07. Date Issued: 12/1/2010 Judge: Opinion by GOEKE HEADNOTE XX. Reference(s): Code Sec. 1221 ; Code Sec. 1401 ; Code Sec. 61 ; Code Sec. 6651 ; Code Sec. 7491 Syllabus Official Tax Court Syllabus Counsel Wendell V. and Sharon T. Garrison, pro sese. Roger W. Bracken, for respondent. Opinion by GOEKE MEMORANDUM FINDINGS OF FACT AND OPINION Respondent determined deficiencies in petitioners’ Federal income tax and additions to tax under section 6651(a)(1) for 1998, 1999, and 2000. 1 After concessions, the issues remaining for decision are: 2 (1) Whether petitioners’ gains from sales of real property during tax years 1998-2000 were ordinary income or capital gain; (2) whether petitioners are liable for self-employment taxes; (3) whether petitioners are entitled to deduct additional costs associated with the gross income received from purchasing and selling real property; (4) whether petitioners are liable for income tax on dividends received; (5) whether petitioners are liable for income tax on interest received in 1998; (6) whether petitioners must reduce their itemized deductions for all years and their child tax credit for 1998; (7) whether petitioners are liable for a failure to timely file addition to tax pursuant to section 6651(a)(1). We resolve these issues against petitioners, except we hold that respondent has not carried the burden of proof with respect to the increased deficiencies and additions to tax asserted in his amended answer. FINDINGS OF FACT Petitioners resided in Maryland when they filed their petitions. On March 22, 2002, petitioners filed their delinquent joint Federal income tax returns for tax years 1998, 1999, and 2000. On June 8, 2007, respondent issued a notice of deficiency (notice). On September 4, 2007, petitioners timely filed their petitions in this Court for tax years 1998, 1999, and 2000. The notice mailed to petitioners reflects, among other adjustments, a recharacterization of petitioners’ real estate transactions. Specifically, respondent classified income from these transactions as ordinary income from a trade or business rather than royalty income, or capital gains as petitioners now claim. 3 Respondent made additional adjustments, some resulting from his recharacterization of the income from real estate sales. The overall adjustments are as follows: 1999 2000 1998 Schedule C: Income $834,000 $604,500 $473,000 Capital gain or loss -0- 27 -0- Self-employment tax 13,240 13,789 16,439 Self-employment tax deduction (6,620) (6,895) (8,220) Cost of goods sold (656,315) (426,000) (212,000) Dividend income 38 38 37 Interest income 50 -0- -0- Schedule E: Royalty income (63,991) (47,121) (73,464) Itemized deductions (44,328) (16,656) 1,478 Exemptions -0- -0- 8,064 During tax years 1998 through 2000, petitioners regularly purchased and sold real estate within short periods. Petitioner husband earned not more than $40,000 annually as a mortgage banker, and petitioners’ purchases and sales of real estate contributed substantially to their income. Many of the properties petitioners purchased were in foreclosure. In 1998 petitioners sold eight parcels of real property. Petitioners did not claim expenses or repairs for any of these properties on their 1998 Form 4797, Sales of Business Property. Petitioners sold all those properties within 2 months of purchase, with one exception. In 1999 and 2000 petitioners sold four parcels of real property each year. Petitioners listed expenses and repairs on their 1999 Form 4797. Petitioners sold each property within 10 weeks of acquiring it. Over the 3 years petitioners did not rent any of the properties before selling them. Trial was held on December 7 and 9, 2009, in Washington, D.C. On March 11, 2009, the Court had granted respondent’s motion for leave to amend the answer. Respondent’s amended answer asserted increased deficiencies and section 6651(a)(1) additions to tax as follows: Original Increased Original Increased sec. 6651(a)(1) sec. 6651(a)(1) Year deficiency deficiency additions to tax additions to tax 1998 $27,118 $69,298 $6,779 $17,324 1999 32,532 84,259 8,133 21,052 2000 65,751 109,348 16,473 35,489 Respondent’s increased deficiencies and additions to tax are based on property sale proceeds not included in the notice of deficiency. Those proceeds increased petitioners’ self- employment taxes and their adjusted gross income. The changes to petitioners’ adjusted gross income resulted in increased self- employment tax deductions and reductions in itemized deductions and exemptions. On his posttrial brief, respondent again revised his position regarding unreported income from petitioners’ real estate transactions as follows (the amounts in the notice of deficiency are shown as well): Notice of deficiency net real estate Revised self- income adjustment to employment income self employment per respondent’s Year income brief 1998 $177,685 $196.138.79 1999 178,729 112,505.08 2000 261,000 196,607.57 At trial petitioners submitted Forms 1040X, Amended U.S. Individual Income Tax Return, for these years. Petitioners also entered into the record Forms 4797 which listed the costs of repairs and expenses for real estate. Both sets of documents were admitted to help the Court understand petitioner husband’s testimony. However, petitioners produced no receipts, invoices, or any other evidence to substantiate the expenses petitioners claim they paid on their real estate ventures. Respondent submitted deeds and Forms HUD-1, Settlement Statement, for the properties petitioners purchased and sold during the years at issue and used these documents to calculate the gains by subtracting from sale proceeds the purchase and settlement costs. OPINION I. Burden of Proof The taxpayer bears the burden of proving by a preponderance of the evidence that the Commissioner’s determinations in the notice of deficiency are incorrect. Rule 142(a); Welch v. Helvering, 290 U.S. 111, 115 [12 AFTR 1456] (1933). Deductions are a matter of legislative grace, and a taxpayer bears the burden of proving entitlement to any claimed deductions. Rule 142(a)(1); INDOPCO, v. Commissioner, 503 U.S. 79, 84 [69 AFTR 2d 92-694] (1992); New Colonial Ice Co. v. Helvering, 292 U.S. 435, 440 [13 AFTR 1180] (1934). In general, the burden of proof with regard to factual matters rests with the taxpayer. Under section 7491(a), if the taxpayer produces credible evidence with respect to any factual issue relevant to ascertaining the taxpayer’s liability for tax and meets other requirements, the burden of proof shifts from the taxpayer to the Commissioner as to that factual issue. Petitioners have not alleged that section 7491(a) applies or established their compliance with its requirements. Section 6214(a) grants the Court jurisdiction to redetermine a deficiency and to determine whether any additional amounts or any additions to tax should be assessed. Respondent may assert an increased amount under section 6214(a); however, with respect to the increased deficiencies and section 6651(a)(1) additions to tax, respondent bears the burden of proof. After briefing, the increased deficiency respondent seeks is for 1998. Petitioners bear the burden of proof with respect to the deficiencies and additions to tax determined in the deficiency notice. See Rule 142(a). II. Issues A. Capital Gain or Ordinary Income The first issue is whether petitioners are entitled to capital gains treatment for proceeds of their property sales. 4 Respondent argues that the real estate petitioners purchased and sold was held primarily for sale to customers in the ordinary course of petitioners’ trade or business of real estate refurbishment and not for investment. If petitioners held the property primarily for sale to customers in the ordinary course of business, as respondent argues, petitioners’ gains will be treated as ordinary income. 1. Section 1221 Petitioners assert they purchased real estate for the purpose of holding it for investment and with the intent of renting it. Respondent argues that petitioners’ intent was to resell the property. A “capital asset” is broadly defined as property held by the taxpayer, whether or not connected with his or her trade or business, subject to a number of exceptions. Sec. 1221(a). These exceptions include stock in trade or other property of a kind that is properly included in a taxpayer’s inventory and property held primarily for sale to customers in the ordinary course of the taxpayer’s trade or business. Id. The Supreme Court has defined “primarily” as used in this context to mean “principally” or “of first importance”. Malat v. Riddell, 383 U.S. 569, 572 [17 AFTR 2d 604] (1966); Biedenharn Realty Co. v. United States, 526 F.2d 409, 422-423 [37 AFTR 2d 76-679] (5th Cir. 1976). The question of whether property is held primarily for sale to customers in the ordinary course of a taxpayer’s business begins with a factual analysis. Pritchett v. Commissioner, 63 T.C. 149, 162 (1974); Raymond v. Commissioner, T.C. Memo. 2001-96 [TC Memo 2001-96] (citing Cottle v. Commissioner, 89 T.C. 467, 487 (1987)). Typically, the factors in making this determination include: (1) The taxpayer’s purpose in acquiring the property; (2) the purpose for which the property was subsequently held; (3) the taxpayer’s everyday business and the relationship of the income from the property to the total income; (4) the frequency, continuity, and substantiality of sales of property; (5) the extent of developing and improving the property to increase the sales revenue; (6) the extent to which the taxpayer used advertising, promotion, or other activities to increase sales; (7) the use of a business office for the sale of property; (8) the character and degree of supervision or control the taxpayer exercised over any representative selling the property; and (9) the time and effort the taxpayer habitually devoted to the sales. Biedenharn Realty Co. v. United States, supra at 415; United States v. Winthrop, 417 F.2d 905, 910 [24 AFTR 2d 69-5760] (5th Cir. 1969). The Court of Appeals for the Fifth Circuit elaborated that frequency is especially probative because “the presence of frequent sales ordinarily belies the contention that property is being held `for investment’ rather than `for sale.” Suburban Realty Co. v. United States, 615 F.2d 171, 178 [45 AFTR 2d 80-1263] (5th Cir. 1980). 2. Analysis We first examine petitioners’ purpose for acquiring and holding the properties. Petitioner husband testified that sales of the acquired properties resulted from a difficult market and a desire for immediate funds. The record demonstrates that petitioners purchased and sold real estate with the purpose of receiving the maximum gain within a short period. None of the alleged investment properties were leased and only one was held for more than 1 year before being sold. These real estate transactions were entered into regularly and resulted in significant gains during the 3 years at issue. We find that the overall purpose of acquiring the properties was to benefit from the immediate financial gains in selling them as quickly as possible. Although petitioner husband was employed as a mortgage banker during these years, this employment was secondary to the real estate transactions he and his wife pursued. Petitioners’ earnings from the real estate transactions constituted their primary source of income. We also consider the frequency, continuity, and substantiality of petitioners’ property sales. See Rice v. Commissioner, T.C. Memo. 2009-142 [TC Memo 2009-142]. Petitioners engaged in at least 15 sales over 3 years, and most of the sales occurred within 4 months after they purchased the property. Petitioner husband testified: “I’m in the business of buying material, fixing houses and reselling them.” This undertaking involved procuring insurance before the title transfer in order to accelerate the resale. Petitioners did not hold properties as an investment and did not rely on the services of a real estate agent or another third party to select, promote, or sell their properties. Petitioners’ real estate transactions were conducted in the ordinary course of a trade or business and not for investment purposes. Accordingly, we find that respondent correctly treated petitioners’ real estate activities as giving rise to ordinary income derived from a trade or business. 3. Self-Employment Tax and Deduction Section 1401(a) and (b) imposes a tax on the net earnings from self-employment derived from any trade or business carried on by the taxpayer. Sec. 1.1401-1(a), Income Tax Regs. The term “trade or business” has the same meaning under section 1402(a), defining “net earnings from self-employment”, as under section 162. Petitioners were engaged in the trade or business of purchasing and selling real property during the years at issue. On the basis of our finding that petitioners earned income in their real estate trade or business, they are subject to tax on their net earnings under section 1401 and to a deduction under section 164(f). 4. Adjustment of the Cost of Goods Sold Section 6001 requires a taxpayer to keep records or render statements sufficient to establish his gross income, deductions, and credits. Sec. 1.6001-1(a), Income Tax Regs. The income of a sole proprietorship must be included in calculating the income and tax liabilities of the individual owning the business. Sec. 61(a)(2). Respondent argues that petitioners were in the business of renovating properties. Respondent describes petitioners’ regular business activity as finding, purchasing, renovating, and selling foreclosed properties, and respondent allowed expenses for settlement and purchase costs. Petitioner husband explained that the renovation process required procuring insurance, purchasing materials, and hiring additional labor to assist with the repairs and improvements. Notwithstanding the description of these activities, petitioners failed to produce any receipts or other reliable basis for fixing the amounts of repairs or other expenditures incurred during their renovation activities. We therefore find that we cannot approximate allowable amounts for petitioners’ reported repairs and expenditures because petitioners provided nothing on which we could rationally base an estimate. However, to the extent respondent seeks additional deficiencies, respondent has not shown that petitioners actually realized net gains from sales of real estate as asserted in his amended answer, and we do not uphold the increased deficiencies sought for 1998. We note that on brief respondent asserts smaller amounts of gains and self-employment income than in the notice of deficiency for 1999 and 2000. B. Miscellaneous Issues 1. Dividend Income Under section 61(a), gross income means all income from whatever source derived including dividends. Sec. 61(a)(7). During tax years 1998, 1999, and 2000, petitioners received dividends of $38, $38, and $37, respectively, from their stock in AT&T. Petitioners introduced no evidence to contradict these adjustments, and, accordingly, respondent’s determination will be sustained. 2. Interest Income Under section 61(a)(4), gross income includes interest. For tax year 1998, petitioners reported no interest income. Petitioners introduced no evidence to contradict respondent’s determination that they received interest income in 1998. Petitioners have not met their burden, and respondent’s determination is sustained. 3. Itemized Deduction Petitioners claimed various itemized deductions including taxes, mortgage interest, charitable contributions, dependency exemption deductions, and the child tax credit. Respondent allowed mortgage interest expenses for years 1998-2000 but adjusted petitioners’ dependency exemption deductions, itemized deductions, and child tax credit. Petitioners’ entitlement to other itemized deductions for each year was automatically adjusted on the basis of respondent’s calculations of their adjusted gross income. Petitioners failed to produce receipts, expense reports, or other records indicating that they qualified for deductions in excess of the amounts respondent allowed, and petitioners are not entitled to additional deductions. C. Section 6651(a)(1) Addition to Tax Section 6651(a)(1) imposes an addition to tax equal to 5 percent of the amount required to be shown as tax on the return. An additional 5 percent is imposed for each additional month or fraction thereof during which the failure to file continues, but not to exceed 25 percent in the aggregate. Id. Under section 7491(c), the Commissioner must come forward with sufficient evidence to show that an addition to tax is appropriate but need not introduce evidence regarding reasonable cause or similar provisions. Higbee v. Commissioner, 116 T.C. 438, 446 (2001). The burden of proof for the amounts included in the notice of deficiency with respect to the additions to tax remains on petitioners. This addition to tax may be avoided if the failure to file timely was due to reasonable cause and not willful neglect. United States v. Boyle, 469 U.S. 241, 245-246 [55 AFTR 2d 85-1535] (1985). Reasonable cause exists for late filing if the taxpayer exercised ordinary care and prudence but was nevertheless unable to file on time. Sec.(NNN) NNN-NNNN1(c)(1), Proced. & Admin. Regs. Petitioners filed their 1998, 1999, and 2000 Federal income tax returns in 2002. Petitioner husband acknowledged this error at trial and stated he had no excuse to explain the delayed filing. Petitioners did not show reasonable cause or otherwise indicate that the delay resulted from something other than neglect resulting in a failure to comply with filing requirements. We therefore find petitioners did not have reasonable cause and are liable for the section 6651(a)(1) addition to tax for failure to file timely for each year at issue. III. Conclusion Petitioners regularly purchased and sold real estate properties in the ordinary course of their trade or business and are thus liable for the adjustment to their gross income and self-employment taxes. Respondent’s assertion of increased deficiencies and additions to tax based on the inclusion of income in 1998 in excess of the amounts determined in the notice of deficiency fails because respondent has not established that the increased sales were not offset by costs petitioners asserted at trial. Thus, to the extent that respondent increased the amount of income for real property sales during 1998 over the amounts determined in the notice of deficiency, petitioners are not liable for either the increased deficiency or the increased addition to tax. On brief respondent conceded some amounts of self-employment income from real estate sales for 1999 and 2000, and these concessions as listed in the Findings of Fact are accepted. Concerning petitioners’ request for additional expense deductions in 1998, 1999, and 2000, petitioners have not met their burden to establish that they qualify for additional deductions in excess of those allowed. Petitioners are liable for the section 6651(a)(1) additions to tax for 1998, 1999, and 2000 resulting from the above analysis. To reflect the foregoing, Decisions will be entered under Rule 155.

Expert again...The business purpose behind the flips will drive the tax treatment. With investors, it is also possible that your client entity can be a dealer, and take ordinary income payout, while the investors can receive capital gains treatment (they may be only involved in one flip, and then only as an investor...).

This is another question concerning the above. I will pay you for this. How do I handle the entity part of this problem? In other words, how do I support the type of entity? Should I list several? I cannot imagine there is tax code to support the recommended entities. Please advise. Thanks.

If you accept that a volume of flips converts the real property from capital gain property to ordinary income property as inventory, if the volume is in the entity, then that taint could be applied to every owner and every purchase. It also means that one group of investors is in on every deal. It also has some financing issues, since banks will want 20% and commercial mortgage rates unless your enterprise is capitalized to do this without mortgage-based financing. I suggest another route.

The best structure for a number of reasons in an LLC for each flip, with your investor operating as the general partner, probably through his own management company entity. He will clearly be in the business, and can take deductible management fees from the LLC owner entities. Each flip is owned by a number of persons, who participate in that flip on its own. They could get capital gain treatment if the flip takes longer than a year. With separate entities, I think limited investors who want to do multiple deals could get capital gain treatment, as they would be passive investors. And their risk is limited to the flip they are in.

My theory is that each stands on its own. That an investor could chose to invest in multiple LLC's or just one. That the flip proceeds at the entity level would be capital, since it's just one flip. That the investors, passively, invest in one activity. They could do it multiple times, but I think the removal from management makes them passive and might be enough to establish capital gain treatment (only one house to be sold).

This may not meet your model perfectly. People are starting businesses with TV shows like 'Flip this House' or similar as a model. Those shows never go into the tax treatment, but paint the picture they want of potential profits. If you have one driving party and a group of recurring investors for the flips, I don't believe capital gain treatment will be possible for one entity and multiple flips.

I will be glad to expand on the entity choice if the deals will be offered to different investors, since that model makes some sense, but would require LLC's for each, soliciting investors for each flip, etc. Mortgage financing could be easier, as the real property could be financed by one investor with mortgage money that could be contributed to the LLC.

Let me know if you can clear up the 'circle of friends' investor pool, and I will be glad to expand the research for you.

One entity for real estate flips is LLC. Everyone gets limited liability protection (good for risks in rehabs - people get hurt on site). S corp would work, too, but distributions limited to pro rata for earnings. LLC is best, XXXXX XXXXX pockets' can take out any distribution warranted, and leave returns for limiteds.

Returns will be ordinary income in any scenario, since the rehab properties are inventory.

You want a pass through entity to distribute profits out, and your main investor will be doing multiple flips, turning capital gains into ordinary income due to 1221. Just had to recap before I cover your next issues.

LLC as recommended entity offers profit flexibility since LLC as S corp would require pro rata distributions to avoid constructive dividend issues. S corps have to be monitored to insure equal distributions. Even unequal compensation, which would be in your case, could cause assertion of constructive dividends by IRS. http://www.fogelcpa.com/documents/constructivedividend.pdf is a good article on the subject.

An LLC as partnership would not have that limitation, and income/loss/capital can be agreed to as part of the owners' agreement. It should mirror a partnership agreement in this instance.

With an LLC as partnership, your general 'deep pockets' partner can take a management fee, wage, and other pay, leaving the potential for capital gain distributions for the limiteds. You could distribute out the gains on sale to the partners, who could retain capital gain treatment for their pieces, since they have no say in management as outlined earlier.

Okay, now I am confused. Originally, you indicated it should be an LLC as a partnership. Now you are talking about an S Corporation. Do me a favor, please. Please write the client letter in response to the original problem. I promise I will not use it. However, I think I will have a better idea of what you are trying to convey if you do that for me. Thanks.

You asked me to research the best entity for your new venture, real estate rehabs and flips. Your intent is to manage the business, provide financing and management, and invite equity investors to share in the profits. You are expecting to do multiple deals, and are hoping that capital gain treatment would allow for lower tax cost on the profits.

There are a few factors that complicate the tax treatment. One is the volume of flips you plan to undertake. The second is the involvement of your investors.

IRS Section 1221 (a) requires ordinary income treatment of the flip gains as the homes being rehabilitated are to be treated as inventory (since there are multiples). One property in the entity at a time could still get the tax treatment you want, but they would have to be held for more than twelve months to obtain long term capital gain treatment.

Since you will be taking management fees and other distributions in addition to a share of profits, and are not involving your investors in management, your entity choices are limited to a limited partnership (LP) or a limited liability company (LLC) treated as a partnership. Other business entity choices require pro rata distributions to all owners. An LLC is preferable to a limited partnership, since the LLC is afforded more legal protection and now has adequate case law history to protect you from business risks.

You did not mention how the properties will be purchased or controlled, but a new entity likely would have difficulty obtaining financing without cumbersome bank application and approval. If you can provide the financing, the properties can be contributed to the entity for legal protection during the rehab and sale processes.

Please advise how we can assist as the project moves forward. As always, I appreciate the opportunity to be of service.

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